Practical Deoxygenation of Oxazole N-Oxides by PCl3/Collidine

Practical Deoxygenation of Oxazole N-Oxides by PCl3/Collidine Full article

Journal

Synthesis-Stuttgart
ISSN: 1437-210X , E-ISSN: 0039-7881

Output data

Year: 2018, Volume: 51, Number: 02, Pages: 414-420 Pages count : 7 DOI: 10.1055/s-0037-1610278

Authors

Shirinian Valerii Z. ¹ , Lonshakov Ilya A. ² , Zakharov Alexey V. ¹ , Lvov Andrey G. ¹ , Krayushkin Mikhail M. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
2	Mendeleev University of Chemical Technology of Russia

A new chemoselective method for the synthesis of 2-aryl-1,3-oxazoles by deoxygenation of the corresponding N-oxides has been developed. As the deoxygenation reagent, a previously unknown complex of collidine with phosphorus trichloride in a 2:1 ratio has been used. The developed method enabled the preparation of a wide range of 2-aryl-1,3-oxazoles comprising various functional groups in good yields. The advantage of this reagent is its tolerance to nitro, methyl, hydroxyl, formyl, and acetyl groups, and double bonds. Due to chemoselectivity and availability of reagents, the method may be used for deoxygenation of N-oxides of other heterocyclic compounds (thiazole, pyridine, quinoline, etc.).

Shirinian V.Z. , Lonshakov I.A. , Zakharov A.V. , Lvov A.G. , Krayushkin M.M.
Practical Deoxygenation of Oxazole N-Oxides by PCl3/Collidine
Synthesis-Stuttgart. 2018. V.51. N02. P.414-420. DOI: 10.1055/s-0037-1610278 WOS Scopus OpenAlex

Web of science:	WOS:000454937600008
Scopus:	2-s2.0-85059554035
OpenAlex:	W2889563481

DB	Citing
OpenAlex	3
Scopus	3
Web of science	2